


Culture Swap or The One With Sex In Kilts.

by MoonlightIcarus



Series: Bobby Tries New Things [10]
Category: Supernatural
Genre: Anal Sex, Bottoming from the Top, Clothed Sex, Clothing Kink, Coming In Pants, Dirty Talk, Established Relationship, Kilts, Kissing, M/M, Riding, Rough Kissing, Smut, Top Crowley (Supernatural)
Language: English
Status: Completed
Published: 2020-01-14
Updated: 2020-01-14
Packaged: 2021-02-27 06:35:17
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22232650
Author URL: https://archiveofourown.org/users/MoonlightIcarus/pseuds/MoonlightIcarus
Summary: As a special surprise to Crowley Bobby dresses up in a kilt and the full accompanying ensemble, then he rides the King of Hell while they're both fully dressed.Basically Bobby tries topping from the bottom to mixed results.
Relationships: Crowley/Bobby Singer
Series: Bobby Tries New Things [10]
Series URL: https://archiveofourown.org/series/1508930
Comments: 1
Kudos: 23





	Culture Swap or The One With Sex In Kilts.

Bobby wanted to skrew with Crowley. Not in an important way but something that could knock him off his rocker, but that had its limits. There weren't very many things that the king if hell cared about that could he could ruin without inciting the rage of a demon and kickstarting another apocalypse. As with all things it came back to something sex related. There had been a good attempt to find a non sexual activity that could knock him down a peg but nothing was a good balance for him, all the ideas being too much or not enough in his book.

It had actually been when he was putting away his laundry that he got the full idea for his plan. The suit he wore back from their trip to Scotland was still handing in its suit bag.

Crowley actually kept all the articles of clothing he made somewhere, weather it be because of the sentimentality he had with the object or just becuase he didn't want to destroy it, and then make an entirely new one was unclear and unimportant.

What was important was that Bobby had an idea now. He'd get all dressed up in his suit and then spontaneously fuck the demon out of nowhere. Not really a punishment but he would be left shell shocked from the surprise. That's all he needed really.

But for that to work he had to practice getting dressed. Its sounded so idiotic that he would need to prepare himself to get dressed in a timely manner but that spoke to the obnoxious complexity of the outfit he wanted to wear.

It had too many pieces to it. The kilt itself, and undershirt, a dress shirt that didnt even have buttons on the sleeves and instead required cufflinks, a vest(or a waistcoat as Crowley was so anal about calling it), a coat, a belt, abusidly soft and tight socks that rested just below his knee, garters on said socks that kept them in place and extended to just above the knee, Ghillie Brogues that needed to be wrapped behind the ankle and calf before being tied in the front. Lastly came the sporran that he jsut needed to let rest on his hips and he was good to go.

An entire week had been devoted to leaning how to get dressed up like this in a timely manner. The first two attempts he has taken too long and he had to throw it all off of himself before Crowley saw and ruined his plan. The next time it had taken him nearly forty minutes and when he went to see how it turned out he could firmly say he looked like shit. The fourth try took just as long but it looked better. Number five was quicker and was also an improvement in appearance. Crowley was around for the entirety of the next day which meant he couldn't try it on again, but he did subtly check online to make sure she was doing everything correctly and in the most efficent way.

Turns out he wasn't, so on Sunday he followed the suggestions online and had it done in less than twenty-five minutes while looking immaculate if he was being a little vain with himself.

Now it had turned Monday and Bobby got dressed again but he was slower this time around. He wanted to startle the demon, and then ruin him and his perfect Armai suit, but that meant going in with no lube on Crowley's monster cock. Over the months they'd been together as a couples he'd gotten better at taking his mighty girth, but he still had his limits. So when Bobby got dressed he did so with a large dildo shoved up his ass.

Maneuvering became more troublesome with the hindrance, but if he stretched himself out after he had gotten dressed there would be lube everywhere and he probably would have messed up his suit.

The dildo was going to be left inside of his ass until Crowley showed up, at which point he would pull it out of himself and skrew the demon. The dildo was actually from the completely unsubtle black leather crate that was kept in the bedroom. As Crowley put it "It's there in case you ever feel like spicing things up." Which would make sense if the demon didnt suggest new things for them to try in bed on an almost daily basis. But finally there was a use for the chest besides just being a reminder of all the ways his life has changed since he started romancing with the enemy.

Crowley made his presence in the living room known with the regular clicking of his dress shoes against the hardwood flooring. It was show time, so Bobby pulled the dildo oit of himself and tried his best to ignore how gaping and open he now felt as he walked into the other room.

Bobby didnt speak he only acted, pressing his hands against Crowley's shoulders and pushing him down onto the couch behind him.

With deft hands his pants were opened and his underwear wash pushed down and tucked behind his balls. It only look a few light, touches to get the other man hard. Bobby was delight to their mouths together to silence the demon while he sat on his now exposed crotch and let his cock slip into the crease of his ass. He had to remove a had from one of Crowley'sshoulder to get any of the fabric from the kilt out from between them, though the other likely didn't notice as he was currently enraptured by the smooth grind against his cock.

Bobby could feel him attempt to pull away and ask questions, but he jsut doubled down in his work, pushing against the back of his neck forcing then closer together as he pulled himself up before using his free hand to line up Crowley's cock with his entrance.

As the prince albert adorning the head entered he nearly covered up the desperate groan that left his lips.

He was forced to go so annoyingly slowly becuase the only lu recant he got was that currently leaking from his hole. Crowley wouldn't speak so long as he continued moving, but that involved going at a constant pace regardless of how fast or slow that pace was that he set for himself. 

Bottoming out seemed like an impossible goal no matter how long he was at his task. The familiar stretch of his sphincter had an unusual burn to it that he was slowly growing addicted to. At final push that left his rest his ass back down on Crowley's pelvis, Bobby threw his head back and moaned out at the feeling.

The moment of self fulfillment didnt last long. Quickly their mouths were clashing together just as they had been before and Bobby started to pull up off of Crowley jsut the slightest amount sk he could decent back down on him. It was a pleasant cycle that grew longer each time as he rose higher up on each successive attempt.

He was so desperate to get a good deep breath in while going about the strenuous task of riding his hung like a horse boyfriend, but he couldn't manage it. The suit was tight, especially around his ribs and abdomen, so his whole abdomen was compressed and reduced his lung capacity. It was exhausting that he could get in a good breath.

Bobby must have slowed down without noticing, becuase in his struggle to breath Crowley thrust up into his pressing his prince albert right against the hunter's prostate getting a yelp out of the mostly silent man.

Crowley's hands had descended down to the back of his neck and the small of his back where they both pushed him closer to the demon. "Oh darling this has been such a wonderful surprise but you look so delishouly fuckabkw that I cant jait sit idly by while you have your fun...of course that doesn'teen I'll be doing all the work."

The hand on his neck drifted down to his shoulders, restoring somenof his range of movement, but the hand on his back wouldn't budge keeping him close to Crowley, forcing to to feel the scratch of the flannel kilt against his weeping erection.

His actions were now more himping and grinding that actually riding in long strokes as he had been before. Crowley was careful to prevent him from moving away while he toyed with him.

The scratch of fabric had him coming quickly from the slight change in position, and with nowhere to go it jsut pooled near the head of his cock.

In that aftermath Bobby leaned heavily on Crowley who started to fucked him for real.

"Darling, thank you for this lovingly well dressed treat."

**Author's Note:**

> Please leave comments.


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